Chapter 5: "The Paradox of Risk"
Chapter 5: "The Paradox of Risk"
Now that we've established the scientific method as our framework for thinking clearly about poker and travel, let's tackle one of the most counterintuitive truths I've discovered: The biggest risk in both poker and travel isn't losing money—it's missing the opportunity for extraordinary experiences.
This is the paradox of risk: Playing it safe is often the riskiest strategy of all.
Most people think about risk as the chance of losing something they have. But Feynman-influenced thinking reveals a deeper truth: The greatest risk is often the chance of never gaining something you could have had.
This chapter is about how I learned to calculate risks not just mathematically, but holistically—considering not just what I might lose, but what I might never experience if I don't take the leap.
Poker taught me that most people are terrible at assessing actual risk versus perceived risk. They'll agonize over a $100 bet with 70% equity, but casually buy a lottery ticket with 0.0001% equity. They'll fold winning hands because they're afraid of variance, but call with losing hands because "it feels right."
Here's a specific example: I once folded pocket queens pre-flop in a tournament because I was "protecting my stack." I calculated that I was probably a 4-to-1 favorite, but I was scared of the 20% chance I'd lose. What I failed to calculate was the risk of never building a stack worth protecting.
That fold haunted me for months. Not because I lost money—I didn't lose anything in the immediate sense. But I lost opportunity. I lost the chance to accumulate chips when I had a mathematical advantage. I lost momentum, confidence, and position in the tournament.
That's when I realized: The risk of missing opportunities is often greater than the risk of failing when you take them.
Good poker players learn to embrace calculated risks, to be comfortable with uncertainty, to make decisions based on long-term expected value rather than short-term fear of loss.
Travel taught me that the same principle applies to life decisions. Most people overestimate the risks of adventure and underestimate the risks of playing it safe.
Take that 110-day world cruise. Everyone focused on the obvious risks: the cost, the time away from "normal life," the possibility of not enjoying it, the logistics of being away for nearly four months. But what about the risk of not going?
The risk of not going included: Never experiencing that kind of extended time perspective, missing the chance to see how I handled sustained travel, losing the opportunity to deepen relationships through shared adventure, and simply never knowing what I was capable of.
When Sarah suggested the Disney Magic cruise, I had to weigh the "risk" of spending money on something that might feel too structured against the risk of dismissing an experience without giving it a fair chance. The mathematical cost was clear. The opportunity cost of closed-mindedness was incalculable.
Here's the paradox: The experiences that scared me most—the ones that felt like the biggest risks—often turned out to be the most valuable. Not because they always went perfectly, but because they taught me things I couldn't learn any other way.
Both poker and travel have taught me to recognize "all-in moments"—situations where the risk of not committing fully is greater than the risk of committing completely.
In poker, going all-in with pocket aces isn't really a risk—it's just the logical conclusion of having the best possible starting hand. The real risk would be playing them timidly and letting worse hands draw out on you.
The Fair Isle trip was one of those all-in travel moments. Getting to this remote Scottish island required multiple flights, perfect weather coordination, and a leap of faith that something meaningful would happen in a place where "nothing" was supposedly happening.
The conventional risk assessment said: "This is expensive, logistically complicated, and you might be bored." But the deeper risk assessment said: "You might miss the chance to experience total solitude in one of the world's most remote beautiful places."
Going all-in on Fair Isle meant committing to the experience completely—not having backup plans, not checking emails constantly, not treating it as just another stamp in the passport. Full commitment to presence.
That total commitment transformed what could have been an expensive sightseeing trip into a profound lesson about solitude, presence, and finding meaning in simplicity. But only because I was willing to risk being completely present rather than hedging with distraction.
But knowing when to go all-in is only half the equation. Equally important is knowing when to fold—when to abandon plans that aren't working, when to pivot based on new information.
I remember a trip to Eastern Europe that I'd planned meticulously. Six months of research, detailed itineraries, hotel bookings, restaurant reservations. But three days in, I realized I was trying to force an experience that wasn't authentic to who I'd become as a traveler.
The old Ed would have powered through, determined to get value from all that planning. But poker teaches you that sunk costs are irrelevant to future decisions. The money spent on planning was gone regardless. The question was: What would create the most value going forward?
It's like folding a hand where you've already invested two bets. Those bets are gone. The only question is whether calling the third bet has positive expected value based on current information.
So I folded. Literally. I abandoned most of the itinerary and spent the remaining time in just two cities, focusing on depth over breadth, on unstructured exploration over scheduled activities.
That trip became one of the most memorable precisely because I was willing to risk "wasting" the planning and embrace what the situation actually called for.
Here's the deepest paradox I've discovered about risk: The people who seem to take the biggest risks—traveling to remote places, playing high-stakes poker, making unconventional life choices—are often taking smaller risks than people who play it safe.
Because they've learned to calculate risks accurately. They've developed skills, knowledge, and confidence that make seemingly dangerous choices actually quite safe. Meanwhile, people who avoid all apparent risks often face the much larger risk of an unlived life.
My military background taught me that preparation reduces risk. Poker taught me that calculated aggression reduces risk. Travel taught me that flexibility and adaptability reduce risk.
When I booked that first Alaska cruise, it felt like a huge risk. When I committed to 110 days at sea, it felt enormous. When I decided to spend 2023 traveling extensively post-pandemic, it felt almost reckless.
But each experience built skills, confidence, and understanding that made the next "risk" actually safer. I wasn't becoming more reckless—I was becoming more capable.
So what's the practical takeaway from the paradox of risk? It's this: Don't let fear of losing what you have prevent you from gaining what you could have. Calculate risks honestly, but include opportunity costs in your calculations.
Risk assessment is a skill that improves with practice. The more calculated risks you take, the better you become at distinguishing real dangers from imaginary ones, genuine opportunities from fool's errands.
But here's what I learned beyond just taking smart risks: You need systems for managing them. You need frameworks for making these decisions consistently, not just when inspiration strikes or desperation forces your hand.
In our next chapter, we'll explore how I developed those systems—how I learned to engineer edges in both poker and travel, rather than just hoping for good luck.
🧭 Chapter 5 Navigation Complete
"The biggest risk isn't losing what you have—it's never discovering what you're capable of having."
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